Planning My Marriage to My GF w/ Ali Kolbert | WHGS Ep. 300 SPECTACULAR

We're Having Gay Sex

Ashley Gavin & Studio71

Society & Culture, Comedy Interviews, Comedy

4.8 • 2.8K Ratings

🗓️ 1 December 2025

⏱️ 70 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

This episode is a MILESTONE, listener! To celebrate the 300th episode of WHGS, we are joined by beloved co-host and dear friend Ali Kolbert to bring things full circle: this podcast started alongside Ashley’s relationship with Jen, so it’s only right that we have another life milestone alongside an episode milestone! We strategize how Ashley should propose to her girlfriend, and even manage to fit in discussions about relationship mementos, intimacy kink, shadow work, boob reductions, and the powerful will-they-won’t-they of lesbian relationships. Enjoy, and thanks for all of your support through 300 EPISODES OF WHGS!!! FOLLOW ASHLEY GAVIN @ashgavs TikTok: https://www.tiktok.com/@ashgavscomedy Instagram: https://www.instagram.com/ashgavs/ YouTube: https://www.youtube.com/@ashgavs Twitter: https://twitter.com/ashgavs Tour Dates & Newsletter: https://www.ashleygavin.com/#dates FOLLOW ALI KOLBERT @alikolbert TikTok: https://www.tiktok.com/@alikolbert Instagram: https://www.instagram.com/alikolbert/ Twitter: https://x.com/alikolbert Tour Dates & Podcasts: https://www.alikolbert.com/shows SUPPORT OUR PODCAST: Watch this UNCUT: https://www.patreon.com/WHGS Merch: https://shop.merchcentral.com/collections/ashley-gavin Watch on this YouTube: https://youtu.be/YiGHfBcsyaM PRODUCED BY SWETSHOP: Instagram: https://www.instagram.com/swetshop.tv/ Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0	I am gonna ask Jen to marry me.
0:01.6	You are?
0:02.4	Yes.
0:23.4	Can Jen hear this right now? She's not gonna listen. I guess everyone will know except Jen. Everyone will know except Jen. But like no one's gonna come up to Jen? Don't ruin it. Okay, so when are you gonna... You're making some good points. But when are you gonna do it? Where are you gonna do it? Well, this is what I wanted to talk about. And we're going to publish the plan online.
0:21.7	We're going to do it? Where are you going to do it? Well, this is what I wanted to talk about.
0:23.4	And we're going to publish the plan online.
0:24.6	We're going to publish a plan.
0:26.1	Interesting.
0:27.1	We're going to publish it. Really fun one with Ali Allie Colbert.
0:39.3	Kind of like, kind of deep.
0:42.3	Kind of a deep episode with Allie Colbert and I share some news.
0:46.6	I haven't had news in a long time.
0:48.4	I've just been kind of hosting, but I have some news on this episode.
0:51.6	We just reconnect as friends because when you're a comedian,
0:55.1	the only time you can see your friend is on a podcast. Gotta make it into content. Yeah,
1:00.3	and it's a fun one. We also get into like some open relationship stuff and getting over X's.
1:09.7	Anyway, the bonus episodes are also really fun.
1:11.9	Patreon.com slash WHDS.
1:14.1	There's four a month for $10, $2 a month for five,
1:17.4	and then even for just three bucks,
1:18.7	you get my weekly live stream.
1:19.9	I mean, that's pretty crazy of my stand-up.
	...

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